Experiment 2

2.1 Title: Preparation of aspirin

2.2 Objective
: to prepare acetylsalicylic acid, commonly known as ‘aspirin’

2.3 Theory:

It is the most widely used analgesic at the present time. It is commonly prescribed
alone or with other drugs for the treatment of headache, cold, influenza, arthritis etc.
Aspirin can be prepared by the acetylation of salicylic acid with acetyl chloride or
acetic anhydride in the presence of catalytic amounts of pyridine or mineral acid.
Aspirin is a white crystalline solid with a melting point of about 135 oC. The
compound is stable in dry air but gradually hydrolyzes to salicylic and acetic acids in
the presence of moisture.
In that experiment we were synthesized aspirin (acetylsalicylic acid, C9H8O4),
purified it, and determined the percent yield. The purity of the product had been
confirmed by qualitative analysis and by measuring its melting point range.
The esterification of a phenol is best carried out by treating it with an acid anhydride
or acid chloride.
The reaction that was used for the synthesis is shown below.

C7H6O3 + C4H6O3 ------> C9H8O4 + C2H4O2

Salicylic acid Aspirin
(138.13 g/mol) (180.17 g/mol)

Acetylsalicylic acid (ASA), which is being sold under the trade name
"aspirin"

is synthesized by the conversion of Salicylic acid (SA) to Acetylsalicylic acid

(ASA)

using acetic anhydride in the presence of sulpheric acid or phosphoric acid

acting as a catalyst.
The balanced reaction mechanism is as follows;

Step 1: Sodium hydroxide is added to phenol in order to obtain sodium

phenoxide ion.

C6H5OH + NaOH → C6H5NaO + H2O

Step 2: Now under the high temperature and and pressure allow phenoxide ion
is added to react with carbon dioxide gas to give sodium salicyclicate.

C6H5NaO + CO2 → C7H5O3Na

Step 3: hydrogen is added to sodium salicyclicate to give salicylic acid and

sodium.

C7H5O3Na + H → C7H6O3 + Na

Step 4: reaction of salicylic acid with acetic anhydride in presence of sulphuric

acid as a catalyst will yield an aspirin as a product and acetic acid as a by
product.

C7H6O3 + C4H6O3 → C9H8O4 + C2H4O2

 2.4 Chemicals and Apparatus
;Salicylic acid ; beaker
;acetic anhydride ; round bottom flask

;H2SO4 ;spatula

;test tube ;funnel

;test tube holder ;filter paper
;water bath ;Alumminium foil
;measuring cylinder
; balance.

2.5 Procedure:
1.0 grams of salicylic acid, 2.5 mL of acetic anhydride and 3 drops
of concentrated sulpheric acid were placed into a 25 mL test tube. A hot
water bath was prepared by

placing a 250 mL beaker on a hot plate with a thermometer to monitor

temperature.

The 25 mL test tube with the mixture of salicylic acid, acetic anhydride, and
phosphoric

acid was partially submerged in the water bath and heated for 10 minutes
until vapors ceased to

be released. After 10 minutes of heating the submerged test tube passed,it

was added to a beaker containing 30 ml of water. The beaker was left to
cool to room temperature before being placed

in an ice bath for a few minutes to allow crystallization to occur. A suction

filtration was set up and

the mixture was filtered via suction filtration. Once the liquid had been
drawn out of the

mixture, the crystals were washed with 5 mL of cold, distilled water. This
was repeated once

more. The suction filtration apparatus was left on for several minutes to aid
in the drying of the
solid product before it was weighed and recorded. After all the percentage
yield was calculated from the measured actual yield and theoretical yield.

2.6 DATA
Qualitative Data:

The boiling chips (calcium carbonate) were white, opaque

crystals. The acetic anhydride was a clear solution with a vinegar-like
odour. The salicylic acid was a find, white solid powder. The ethanol
was a clear solution with an odour similar to strong alcohol. The
sulfuric acid was a clear solution with a strong odour when heated.
The aspirin (acetylsalicylic acid) was a white, solid powder.

When the acetic anhydride and salicylic acid were mixed, they
produced a white, powdery solution. When the sulfuric acid was
added to this solution, it turned clear and was warm. Upon heating
the solution and adding water, puffs of smoke were produced. When
the solution cooled and the “scratching” method was used, a white
precipitate formed.

Since both acetic anhydride and salicylic acid have a coefficient of 1,

the smaller number is the limiting reactant. Therefore, salicylic acid is
the limiting reactant of the reaction. The theoretical yield of aspirin is
calculated by converting the mass of the limiting reactant to grams of
aspirin.
 2.1 Table of Quantitative Data of Preparation of Asprin

Mass of salicylic acid used (g) 1.00g

Drops of sulpheric acid used 3 drop

Volume acetic acidanhydride used (ml) 2.5 ml

Mass of filter paper (g) 2.6 g

Mass of filter paper and asprin(g) 32g

Mass of purified aspirin product (g) 29.4g

CALCULATION

 From the given value above;

n(C7H6O3)= m(C7H6O3) / M(C7H6O3)

=1g/138.13 g/mol = 0.0072 mol

The ratio of mole of C7H6O3 to C9H8O4 is 1:1 that means 1

mole of salicyclic acid gives 1 mole of asprin.

From the above that;

1mol of C7H6O3 → 1mol of C9H8O4

0.0072mol of C7H6O3 → ?
 So let us take x for unknown value and cross product the given
value.

1mol*x = 1mol* 0.0072mol

X= 0.0072mol.

Let us find the mass of aspirin(m of aspirin)

m of aspirin = n of aspirin X M of aspirin

= 0.0072mol* 180.17 g/mol = 1.3 gram

This is the theoretical yield of asprin.

% yield of aspirin = actual yield of aspirin divided by its

theoretical yield multiplied by 100.

The actual yield of aspirin is the measured weight of aspirin

which is equal to 29.4 gram.

% yield = (29.4g/1.3g) X 100 = 2262%

2.7 DISCUSSION

The active metabolite ingredient in acetylsalicylic acid (aspirin) is

salicylic acid.

Salicylic acid is toxic in large quantities but in small doses can be

useful for food preservatives and as an antiseptic.
 Sulfuric acid is used as a catalyst to speed up the reaction.

Limiting reactants are important in chemical reactions because a

reaction cannot proceed without all of the reactants. That is to say, a
reaction can only occur until one reactant is used up.

The theoretical yield is the amount of a product formed when the

limiting reactant in completely consumed.

The percent yield is the actual yield of a product given as a

percentage of the theoretical yield.

2.8 CONCLUSSION

The main objective of the preparation of aspirin lab was so produce

aspirin (acetylsalicylic acid) through the reaction of salicylic acid and
acetic anhydride. The methods used included recrystallization and
scratching to produce a precipitate, which was then filtered to remove
any excess moisture. The results displayed a percent yield of 2262%,
from a theoretical yield of about 1.3g of aspirin and an actual yield of
approximately 29.6g of aspirin. Upon completion of the lab, analysis,
and calculations, it is evident that the synthesis of aspirin is possible
using these methods but that the yield was very high due to some
errors.

2.9 ERROR ANALYSIS

The source of error could were been due to the measuring instrument
or due to measuring an aspirin that were not dried. So this resulted
unnecessary percentage yield of aspirin. To get necessary
percentage yield the aspirin must be dried. This make the theoretical
yield less than the actual yield.